Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Deprotonative Silylation of Aromatic C–H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride

Deprotonative Silylation of Aromatic C–H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride
Kanako Nozawa-Kumada, Masanori Shigeno, Isabelle Chataigner, Yoshinori Kondo, Midori Sasaki, Sayuri Osawa
A method for the deprotonative silylation of aromatic C–H bonds has been developed using trifluoromethyltrimethylsilane (CF3SiMe3, Ruppert–Prakash reagent) and a catalytic amount of fluoride. In this reaction, CF3SiMe3 is considered to act as a base and a silicon electrophile. This process is highly tolerant to various functional groups on heteroarenes and benzenes. Furthermore, this method can be applied to the synthesis of trimethylsilyl group-containing analogs of TAC-101, which is a bioactive synthetic retinoid with selective affinity for retinoic acid receptor α (RAR-α) binding. We also report further transformations of the silylated products into useful derivatives.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01525

DOI: 10.1021/acs.joc.7b01525

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